Fatty acids in vegetable oils and their importance

science technique
in cosmetic industry
Aleksandra ZIELISKA*, Izabela Nowak Faculty of Chemistry, Adam Mickiewicz University
in Poznan, Pozna, Poland

Please cite as: CHEMIK 2014, 68, 2, 103110

Introduction Saturated fatty acids

Vegetable oils are liquid vegetable fats that remain in the liquid This group includes fatty acids, which do not contain double
form at room temperature. These lipids are most commonly extracted bonds in the molecule. Under normal conditions, these compounds
from various parts of plants such as seeds, fruits, or plant seedlings. are most often white solids. Fatty acids having a chain of more than
Under the chemical terms they are a combination of triglycerides of 10 aliphatic carbon atoms are non-volatile and insoluble in water [4].
higher saturated and unsaturated fatty acids. In other words, these Among the saturated fatty acids found in vegetable oils are: myristic
compounds are esters of glycerol and higher fatty acids, containing in acid, palmitic, stearic or arachidic acids (Tab.1). Shorter chain fatty
their structure long (low C14:0) aliphatic carbon chains [1] . Vegetable acids (C810) occur in nature only in the form of triglycerides.
oils, depending upon the individual percentages of fat acids in the
molecule, exhibit a variety of properties. Thanks to their beneficial Table 1
influence, especially on the skin, fatty acids are of great importance in Examples of saturated fatty acids
cosmetology, becoming more and more commonly used components Systematic name Common name Formula Symbol
of many cosmetic formulations intended for daily care of the face and
Caprylic acid Octanoic acid CH3(CH2)6COOH C8:0
body. Deficiency in these compounds can cause excessive drying of
the skin. Vegetable oils, serving as a cosmetic base , prevent water Capric acid Decanoic acid CH3(CH2)8COOH C10:0
loss through the skin, mainly by means of making a protective layer
Lauric acid Dodecanoic acid CH3(CH2)10COOH C12:0
on the epidermis. Additionally, they soften the stratum corneum and
reduce inflammation of the skin, thereby weakening the sensation Myristic acid Tetradecanoic acid CH3(CH2)12COOH C14:0
of pain. Furthermore, they play a very important role in the proper - Pentadecanoic acid CH3(CH2)13COOH C15:0
functioning of the human body. Also medicine recognizes the
beneficial effects of vegetable oils , mainly in the biological synthesis Palmitic acid Hexadecanoic acid CH3(CH2)14COOH C16:0
of components of cell membranes or eicosanoids (prostaglandins, Margaric acid Heptadecanoic acid CH3(CH2)15COOH C17:0
prostacyclins , thromboxanes , leukotrienes). Oils are also involved
Stearic acid Octadecanoic acid CH3(CH2)16COOH C18:0
in the transport and oxidation of cholesterol. The absence of these
oils contained in the fatty acids significantly affects vascular fragility, - Nonadecanoic acid CH3(CH2)17COOH C19:0
reduces the immune system workflow, interferes with the clotting
Arachidic acid Eicosanoic acid CH3(CH2)18COOH C20:0
process and also increases the likelihood of the development of
atherosclerosis [2]. Behenic acid Docosanoic acid CH3(CH2)20COOH C22:0

Lignoceric acid Tetracosanoic acid CH3(CH2)22COOH C24:0

Types of fatty acids
The name of Essential Fatty Acids (EFA) was introduced in
1929 and refers to the fatty compounds important for the proper
development and functioning of the human body. Depending
on the presence and the number of bonds, fatty acids can be
classified into saturated and mono-and polyunsaturated (including
the so-called omega-3, omega-6 and omega-9 family) Fig. 1. This
typology is a key parameter determining the usefulness of cosmetic
triglycerides [2, 3].
Fig. 1. Fatty acids types
Corresponding author:
Aleksandra ZIELISKA M.Sc., email: zielinska-aleksandra@wp.pl
Unsaturated fatty acids
The composition of this family includes fatty acids containing
double bonds, which are usually colourless liquids. For most of
them, all double bonds are in the cis positionWhen determining
the position of the double bonds their exact location is pointed
out. The most commonly used for this denotation is the symbol :
delta K, l, m.. , where k, l, m.. indicate the number of the carbon atom
on which there is a double bond, counting from the carboxyl group.
For example, linoleic acid can be denoted as 9,12, which means
that the double bonds are located at the 9 and 12 carbon atoms [4].
Currently, there are two main classes of unsaturated fatty acids, namely
the monounsaturated fatty acids, which include omega-9 fatty acids
(-9 or n-9) and polyunsaturated fatty acids, which include omega- 6
(-6, n-6) and omega- 3 (-3, n-3). Polyunsaturated fatty acids have
in their structure at least two double bonds, and at least 18 carbon
atoms in the alkyl chain. Biological activity of the molecule depends on
the configuration and the specified position of the cis double bonds. It
is worth noting that carbon in -CH3 group is called the omega carbon
and also all the double bonds are separated by at least one methylene
group. The systematic names of unsaturated fatty acids have to provide
the location of a double bond, counting from the carboxyl carbon. For
example, linoleic acid is also called 9, 12-octadecadienoic acid [2].
The so-called essential fatty acids (EFAs) include linoleic acid (LA)
and -linolenic acid (ALA), they are not synthesised in the human body

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 because of the lack of appropriate enzymes. Other polyunsaturated
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fatty acids can be synthesized only if EFA will be delivered with food
and when no enzyme defect would occur in the metabolic pathway.
Linoleic acid is considered the most important of all omega-6 fatty
acids, because it can be obtained with other acids of this group such
as ALA or -linolenic acid (GLA) [14].
The unsaturated fatty acids most important in cosmetology and
medicine include [2, 4]:
monounsaturated fatty acids , containing one double bond, such
as palmitoleinic acid 16:1 ( -7) , oleic acid 18:1 ( -9) , erucic
acid 22:1 ( -9) , nervonic acid 24:1 ( -9)
biunsaturated acids (diene) containing two double bonds , such as
18:2 linoleic acid (-6, LA)
triunsaturated acids (triene), containing three double bonds ,
such as -linolenic acid 18:3 (-3 , ALA) acid, -linolenic acid
18:3 ( -6 , GLA)
tetraunsaturated acids (tetraene) containing four double bonds,
such as arachidonic acid, 20:4 ( -6 -related biogenetically
prostanoids).
The following are most unsaturated fatty acids present in
vegetable oils (Tab. 2 ).
Table 2
Examples of unsaturated fatty acids [4]
free fatty acids on the skin are supposed to be generated as a result
of decomposition of triglycerides by bacteria. On destruction of
the protective barrier or on elevation of the transepidermal loss
of water (TEWL), epidermis produces more lipids in the lamellar
granules of the stratum granulosum. Unfortunately, with age the
reproduction of lamellar granules slows down. It has been shown
that the use of lipids containing fatty acids, in particular those
belonging to omega-6 series, accelerates the reproduction of lipids
in lamellar granules [5]. A lipid barrier forms at the interface between
the stratum granulosum and stratum corneum. At this interface the
lamellar granules form aggregates, their membranes undergo fusion
and the contents of the granules are released in the form of discs and
lamellae (Fig. 2). It should be mentioned that the use of a single lipid
(e.g. cholesterol) on young skin causes a delay in regeneration of the
lipid barrier, but on aged skin it has the opposite effect. The use of
a mixture of three lipids (fatty acids with cholesterol and ceramides)
on the aged skin brings acceleration of regeneration of the lipid
barrier if the dominant component of the cream is cholesterol. On
the young skin a similar effect was observed when any of the three
components dominated at the ratio 3:1:1 [9].
Table 3
Selected lipid components of human sebum [5, 6]

General Numerical Omega Content in %

Common name Systematic name
formula Symbol family Lipids group
Palmitoleic acid (Z)-9-hexadecenoic acid C16H30O2 16:1 7 On the skin surface In sebaceous glands

Oleic acid (Z)-9-octadecenoic acid C18H34O2 18:1 9

Fatty acid triglycerides 19.549.4 24.034.0
Elaidic acid (E)-9-octadecenoic acid C18H34O2 18:1 9
Free fatty acids 7.939.0 -
Petroselinic acid (Z)-6-octadecaenoic acid C18H34O2 18:1 12
Waxes and esters of chole-
Vaccenic acid (E)-11-octadecenoic acid C18H34O2 18:1 7 24.132.1 17.721.5
sterol
Gondoic acid (Z)-11-eicosenoic acid C20H38O2 20:1 9
Squalene 10.113.9 25.631.6
11-(2-cyclopenten-1-yl)
Hydnocarpic acid C16H28O2 - -
undecanoic acid
13-(2-cyklopenten-1-ylo)
Chaulmoogric acid C18H32O2 - -
tridecenoic acid
Erucic acid (Z)-13-docosenoic acid C22H42O2 22:1 9
Nervonic acid (Z)-15-tetracosenoic acid C24H46O2 24:1 9
(Z,Z)-9,12-octadecadie-
Linoleic acid (LA) C18H32O2 18:2 6
noic acid
(Z,Z,Z)-9,12,15-octadeka-
-Linolenic acid(ALA) C18H30O2 18:3 3
trienoic
(Z,Z,Z)-6,9,12-octadeca-
-linolenic acid(GLA) C18H30O2 18:3 6
trienoic acid
(E,E,E)-9,12,15-octadeca-
cis-linolenic acid (CLA) C18H30O2 18:3 3
trienoic acid
(Z,E,Z)-9,11,13-octadeca- Fig. 2. Structures of the stratum corneum and stratum granulosum
Punicic acid C18H30O2 18:3 5 and formation of lipids [58]
trienoic acid
(E,E,E)-9,11,13-octadeca-
Oleostearynic acid C18H30O2 18:3 5
trienoic acid The use of selected fatty acids
(all-Z)-5,8,11,14-eicosate- Linoleic acid occurs most abundantly in sunflower oil, soybean oil,
Arachidonic (AA) C20H32O2 20:4 6
traenoic acid safflower, corn oil, sesame oil, peanut oil, grape seed oil and wheat
Eicosapentaenoic acid (all-Z)- 5,8,11,14,17-icosa- sprout oil. This compound plays a significant role in the skin. in dry
C20H30O2 20:5 3
(EPA), Timnodonic acid pentaenoic acid skin it strengthens the lipid barrier of epidermis, protects against
Docosapentaenoic acid (all-Z)-4,8,12,15,19-doco- transepidermal loss of water and normalises the skin metabolism.
C22H34O2 22:5 3
(DPA), Clupanodonic acid sapentaenoic acid Linoleic acid is a natural component of sebum. In persons with acne
Docosahexaenoic (all-Z)-4,7,10,13,16,19-do- skin, a decrease in LA content in sebum is observed, which leads
C22H32O2 22:6 3
acid(DHA) cosahexaenoic acid to blocked pores and formation of comedos and eczemas. The
(R)-12-hydroxy-(Z)-9-octa- use of linoleic acid for oily skin and problematic skin care leads
Ricinoleic acid C18H34O3 C18:1 9
decenoic acid to improvement of the work of sebaceous glands, unblocking of
pores and decrease in the number of comedos. Moreover, this
The effect of lipids and fatty acids on the skin acid is built in the structure of cell membrane and is also used for
Table 3 presents concentrations of particular components of production of intercellular cement of the skin. These two processes
human sebum on the skin and excreted by sebaceous glands. The are possible thanks to the presence of the enzymatic complex in the

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stratum corneum of epidermis. It should be noted that Linoleic acid the transepidermal water loss so improve the skin moistening,

is also a component of ceramide 1 (so far 7 different ceramides have
been identified in stratum corneum of human skin) [1, 2].
Another important fatty acid from omega-6 series is -linolenic
acid formed as a result of delta-6-desaturase enzyme on the pathway
of metabolic transformations of linoleic acid. Rich natural sources
of GLA are oil from borago officinalis seeds, black currant oil,
evening primrose oil and hemp oil [7]. A representative of omega-3
group, -linolenic acid is found in linseed oil, soybean oil, rapeseed
oil, wheat sprout oil, walnut oil, algae and marine phytoplankton.
Both - and -linolenic acids are physiological components of cell
membranes or mitochondria membranes in human cells. They are
involved in inner and outer cell transport, including transmission
of signals in the neuronal lattice of the brains [14, 7]. The other
acids such as eicosapentaenoic acid (EPA) or docosahexaenoic acid
(DHA) are most often met in fish oil from salmon, cod, herring,
mackerel. There are reasons to suppose that deficiency in essential
unsaturated fatty acids (wrong diet) is related to the incidence
of neoplastic diseases. Omega-3 fatty acids, in particular EPA
and DHA, inhibit development of tumours, growth of neoplastic
tissue and its spreading [10]. It has been proved that these acids
are able to reduce the UV induced post-inflammatory substances.
The fatty acids alleviate the effects of sunburn, stimulate healing
processes and soothe irritations [1]. Eicosanoids are also engaged
in platelet aggregation, chemotaxis and cell growth [11]. The omega
series acids -9 (oleinic), -6 (linolic) and -3 (-linolenic) reduce
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activate regeneration of damaged lipid barrier of the epidermis,
heal inflammations and stabilise the skin metabolism [1]. Essential
Fatty Acids (EFA) also act as receptors stimulating the synthesis of
barrier lipids of the skin and proteins being precursors of the natural
moistening factor [12]. Highly beneficial properties of many fatty
acids have prompted the interest in vegetable oils and their use as
active ingredients of many cosmetic preparations.
Fatty acids in vegetable oils
Unsaturated fatty acids present in vegetable oils are
characterised by high absorbability and antiallergic properties.
Thanks to their beneficial and diverse effects on the skin they have
found wide applications in many branches of industry, in particular
in cosmetic industry and cosmetology, pharmacy and medicine. In
cosmetic industry, vegetable oils are used mainly as the vehicle
for other active ingredients, dissolved or dispersed in oil-water
type emulsions. The most often used essential unsaturated fatty
acids are those from the omega-3, omega-6 and omega-9 series.
The most important among them are 18-carbon acids (C18):
monounsaturated (omega-9) oleic acid, biunsaturated (omega-6)
linoleic acid, including cis-linoleic acid with conjugated double bonds
at positions 3 and 6 (CLA, conjugated-linoleic acid), triunsaturated
(omega-3), -linoleic acid (ALA) and (omega-6), -linoleic acid
(GLA) [13]. Table 4 gives a list of most popular vegetable oils and
the fatty acids they contain [1316].

Table 4
Composition of selected vegetable oils; estimated percentage content of the main components is given in parentheses [1316]
Unsaturated fatty acids
Name saturated fatty acids
Omega-3 Omega-6 Omega-9 Inne
Argan oil PA (12,8); SA (5,8) ALA (0,5) LA (33) OA (46,6)
Chokeberry (seed) oil ALA (8) LA (39) OA (31)
Avocado oil PA(412); SA (2); ARA LA (1020) OA (6080) POA (580)
Peach (pits) oil LA (25) OA (65)
Canola oil PA (6,2) ALA (6,6) LA (21,6) OA (61,3)
MA (<1); LA (5060); GLA
Nigella oil ALA (<0,5) OA (2030) POA (<0,5)
PA (1014); SA (14) (<0,5)
Pumpkin (pumpkin seed) oil PA (815); SA (47) LA(4560) OA (2236)
Wild rose (seeds) MA (<0,5); PA (35); SA (1,52,5) ALA (2832) LA (3550) OA (1318) POA (<0,5)
Pomegranate seeds oil PA (58); SA (26) LA (910) OA(89) PU (6065)
OA (515); EA (6580); EU
Jojoba (liquid wax) oil PA (<3)
(1020)
Cocoa/cocoa butter OA (38)
Wheat sprout oil PA (14); SA (3) ALA (8) LA(57) OA (28)
LAU (4455); MA (621); PA (712); SA (25);
Coconut/coconut butter LA (12) OA (412)
KYL (410); KYN (38)
Safflower oil PA (67,5); SA (<2,5); ARA (<0,5) ALA (10) LA (7085) OA(1525)
Corn oil PA (5565); SA (4) OA (29)
Camelina oil PA (7,8); SA (3) ALA (31,2) LA (23) OA (16,8); EA (12); EU (2,8)
Flax seed oil PA (57); SA (37) ALA (4860) LA (<20) OA (1018)
PA (8,59);
Macadamia oil OA (5761) POA (1420)
SA (33,5)
Raspberries seeds oil PA (2,1); SA (0,9) ALA (23,9) LA (57,5) OA (13,3); EA (0,4)
Meadowfoam seeds oil EA (63); EU (16); C22:1 (17)
Passiflora seeds oil PA (8); SA (2) - ALA (1) LA (77) OA (12)
Almond oil PA (35); SA ALA (1522) - OA (7080)
Neem oil PA (19); SA (15); MA (1) LA (17) OA (48)
Moringa oil OA (85)
LA (3440); GLA
Borago oil PA (9,511,5); SA (24,2) OA (13,518,5)
(1825)
Olive oil PA (11); ARA; BA; MAR ALA (0,7) OA (75)
PA (616); SA (17); ARA (13); BA (25);
Peanuts oil LA (1345) OA (3672)
LCA 13)
Hazelnuts oil PA (47); SA (16) LA (720) OA (6885) POA (<1)
Walnut oil PA (58); SA (26); ARA (<0,5) ALA (<0,8) LA (4565) OA (1421); EA (<0,5) POA (<1)

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Palm oil LAU (51); MA (17); PA (8); SA (2) LA (57) OA (13) -
Papaya seeds oil PA (<16); SA (<5,5) OA (74)
Parsley seeds oil PA; SA ALA (<1) LA (1620) OA (810) PES (6872)
LA (57); GLA
Seabuckthorn oil PA (3033); SA (<1) ALA (30) OA (1418); EA (2) POA (3035)
(35)
Castor oil PA (12); SA (<1,5); ARA (<0,6) ALA (<0,5) LA (57) OA (37); RY (8091) POA (<0,5)
Rice oil PA (15); SA (1,9) ALA (1,1) LA (39,1); AA (0,5) OA (42,5)
Sesame oil PA (910); SA (56) ALA (0,5) LA (4145) OA (4143)
Shea butter/ karit butter SA (3040) OA (4550)
Sunflower oil PA (67); SA (45) ALA (<0,8) LA (6072) OA (1625)
Soybean oil PA (712); SA (26); ARA (2) ALA (410) LA (4858) OA (2030)
Tamanu oil PA (13,5); SA (15,6) ALA (0,2) LA (33,7) OA (35,5)
LA (7075); GLA
Evening primrose oil PA (6,2); SA (1,8) ALA (<2) OA (3,55,4)
(1015)
Grape seeds oil PA; SA ALA (0,5) LA (7285) OA (10)
Cranberry seeds oil PA (5,4); SA (1) ALA (33,8) LA (34,2) OA (24,5) POA (<0,5)
Explanations: PA palmitic; SA stearic; ARA arachidic; BA behenic; LAU lauric; MA myristic; KYL caprylic; KYN caprynic; MAR margaric; LCA lignoceric; ALA -linolenic; LA linolenic ; GLA -linolenic;
POA palmitoleic; OA oleinic; EA eicosenic; EU erucic RY ricinolenic ; PES petroselinic; AA arachidonic; PU punicic

Summary
Vegetable oils are rich source of fatty acids and have been
successfully used in cosmetic products. Because of their oiling,
softening, smoothing and protective properties they are classified
to the group of emollients. They make the skin look smooth and
properly moistened. Recently, much attention has been paid to the
so-called virgin oils whose composition is the same as that inside
the seeds of oleaginous plants. The oil of best quality is obtained
by cold pressing. Vegetable oils obtained by this method contain
a large number of compounds essential for human organism and many
ingredients of high quality cosmetic products for skin and hair care.
The strongest cosmetic activity has been established for unsaturated
fatty acids contained in triglycerides, in particular omega-6 and
omega-3 acids belonging to EFA. For skin care the most important are
the oils with high contents of linoleic acid (-6) and -linolenic acid
(-3), as they are the least comedogenic and restrict the formation
of eczemas. Moreover, both these oils are able to incorporate into
the lipid components of cell membranes, to regenerate damaged lipid
barrier of epidermis and restrict the loss of water. Unsaturated fatty
acids show pronounced healing effect on many dermatoses, like e.g.
atopic skin inflammation and in skin care [7]. They are used as the
base of creams, emulsions, cosmetic milks and creams, ointments,
hair conditioners, brilliantine, cosmetic masks, protective lipstick,
bath fluids, nail varnish and nail cleaners. In cosmeceutics they are
used both as base and active ingredients. Many natural substances
of high biological activity such as vitamins A, D, E, provitamin A and
phospholipids, hormones, steroids and natural dyes dissolve in fatty
acids [17]. All the above mentioned beneficial effects of vegetable
oils and fatty acids they contain illustrate the importance of this group
of ingredients for skin and hair care.
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Translation into English by the Author
* Aleksandra ZIELISKA M.Sc., is a first year student of the Ph.D. stu-
dies in the Faculty of Chemistry at Adam Mickiewicz University in Pozna. She
obtained the Masters degree in 2013, specialisation: Cosmetic Chemistry.
Her scientific interests are focused on cosmetic chemistry, in particular on
chemistry of vegetable and essential oils.
email: zielinska-aleksandra@wp.pl.
Izabela NOWAK (Sc.D.), Associate Professor and Head of the Applied
Chemistry Group. She was granted from TEMPUS a scientific fellowship at
the University of Reading, U.K., in 19921993, where she wrote her M.Sc.
thesis. She received her M.Sc. in chemistry in 1993 from Adam Mickiewicz
University (AMU) in Pozna, Poland, where she also obtained her Ph.D
degree in chemistry in 1996. She received a postdoctoral training at the
Leverhulme Centre for Catalysis in Liverpool. In 2006, she was awarded the
degree of Sc.D.(habilitation) for the research on synthesis, characterization
and catalytic properties of nanoporous materials for the liquid-phase oxidation
processes. American Chemical Society together with IUPAC recognized her
in 2011 as Distinguished Woman in Chemistry/ Chemical Engineering. Her
current scientific interests are focused on synthesis and modification of novel
ordered materials, textural/structural/surface/acid-base/redox properties
of thereafter, heterogeneously catalyzed synthesis of fine and intermediate
chemicals and modern synthesis strategies for cosmetics and cosmeceuticals.
She has published more than 140 papers, 3 patents, and made more than 300
presentations at symposiums and conferences.
email: nowakiza@amu.edu.pl; phone: +48 61 829 15 80

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